2,3-bis(4-hydroxyphenyl)propionitrile

Names

[ Name ]:
2,3-bis(4-hydroxyphenyl)propionitrile

[Synonym ]:
2,3-bis(4-hydroxyphenyl)propionitrile
DPN Diarylpropionitrile SC-4473
2,3-Bis(4-hydroxyphenyl)propanenitrile
Benzenepropanenitrile, 4-hydroxy-α-(4-hydroxyphenyl)-
DPN

Biological Activity

[Description]:

Diarylpropionitrile(DPN) is a non-steroidal estrogen receptor β(ER β) selective ligand.IC50 value:Target: ER β ligandin vitro: Pre-treatment with 1-100 nM DPN significantly decreased neuronal cell death by increasing cell viability through a significant attenuation in the reactive oxygen species level, downregulation of pro-apoptotic activated caspase-3 and Bax, and upregulation of anti-apoptotic Bcl-2, thereby mitigating apoptotic morphological alterations. DPN pre-treatment decreased the expression levels of pro-inflammatory cytokines IL-1β and IL-6 through attenuation of Aβ1-42-induced phosphorylation of mitogen-activated protein kinases JNK and p38. In addition, DPN enhanced ERK1/2 and Akt phosphorylation depressed by Aβ1-42 [1]. ERβ was expressed in RAW264.7 cells, and DPN statistically significantly decreased LPS-induced RANTES production in RAW264.7 cells. Small interfering RNA targeting the ERβ gene inhibited the effect of DPN on RANTES production. In addition, DPN inhibited nuclear translocation and phosphorylation of p65 by inhibiting IκB degradation and thus prohibited the activation of nuclear factor κB (NF-κB) [3].in vivo: DPN treatment during EAE did not attenuate demyelination, only partially improved axon conduction, and did not activate the phosphatidylinositol 3-kinase/serine-threonine-specific protein kinase/mammalian target of rapamycin signaling pathway in ERβ CKO mice [2].

[Related Catalog]:

Signaling Pathways >> Others >> Estrogen Receptor/ERR

Research Areas >> Neurological Disease

[References]

[1]. Suwanna N, et al. Neuroprotective effects of diarylpropionitrile against β-amyloid peptide-induced neurotoxicity in rat cultured cortical neurons. Neurosci Lett. 2014 Aug 22;578:44-9.

[2]. Khalaj AJ, et al. Estrogen receptor (ER) β expression in oligodendrocytes is required for attenuation of clinical disease by an ERβ ligand. Proc Natl Acad Sci U S A. 2013 Nov 19;110(47):19125-30.

[3]. Huang SY, et al. Estrogen receptor β agonist diarylpropionitrile inhibits lipopolysaccharide-induced regulated on activation normal T cell expressed and secreted (RANTES) production in macrophages by repressing nuclear factor κB activation. Fertil Steril.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
449.4±35.0 °C at 760 mmHg

[ Melting Point ]:
203°C

[ Molecular Formula ]:
C₁₅H₁₃NO₂

[ Molecular Weight ]:
239.269

[ Flash Point ]:
225.6±25.9 °C

[ Exact Mass ]:
239.094635

[ PSA ]:
64.25000

[ LogP ]:
2.06

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.640

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UG0900000

CHEMICAL NAME :: Propionitrile, 2,3-bis(p-hydroxyphenyl)

CAS REGISTRY NUMBER :: 1428-67-7

BEILSTEIN REFERENCE NO. :: 3337109

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C15-H13-N-O2

MOLECULAR WEIGHT :: 239.29

WISWESSER LINE NOTATION :: QR DYCN&1R DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1500 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - muscle weakness Behavioral - ataxia

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 112,176,1954

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H319-H400

[ Precautionary Statements ]:
P273-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ RIDADR ]:
UN 3077 9 / PGIII

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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